Stupefy means to render insensitive, lethargic or to confuse and astound. It is often used when referring to people's reactions to narcotics.
"We did not mean to stupefy your mother, ma'am. We did not know we would totally confuse her when we explained the Medicare rules to her."
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Stupefaction
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So- you are asking when to use 'when' in a sentence. When you are asking how to use when in a question, you are already using when in a sentence, because a question actually is a sentence. I like to use when in a sentence whenever I like.
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